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Wednesday Holmes on Growing Their Career as an Independent Artist

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When Squarespace last spoke with illustrator Wednesday Holmes, we explored the origins of their career and relationship with art and activism, with a particular focus on how those spheres of experience intersect with queerness and mental health. 

This month, we caught up with Wednesday again to learn more about their approach to making a living as a successful freelance creative. Find out Wednesday’s philosophy behind developing their portfolio website, their approach to social media management, and their advice for artists hoping to turn their dreams into a creative career. 

Attracting clients with a portfolio website

My Squarespace website gives me the chance to show potential clients what I can deliver as an artist,” Wednesday says. “At the moment, I have about two years worth of client work on my website. This is to give future clients a taste of what I can deliver.” 

Wednesday knows that regularly updating their portfolio website with key projects is an important part of maintaining their site. “I can update my website to show my most recent projects, which,” they add, “in turn, attracts the next client. In this way, I can create the kind of traffic I need to sustain a freelance career. I'm planning to add more landmark projects in the future, so I can showcase more of the iconic brands I've had the chance to work with over the years.”

Advocacy for queer and trans/gender-nonconforming communities, as well as mental health awareness and education, are common themes throughout Wednesday’s artworks. Because those themes and values are such a core part of Wednesday’s brand, they’ve crafted web copy and selected projects that all make those values crystal clear to potential clients. 

“When I take on any project,” Wednesday says, “I like to know that it will fit well with my art style and my ethos as an artist. I like to make art that makes people—specifically queer and trans people—feel good. So when I'm approached, I like to know that the client knows this and wants to nurture that through our collaboration.” 

Engaging with a growing social media following

The ways that Wednesday expresses those themes and values through their distinctive art style has attracted not only a variety of clients over the years, but a thriving social media community. Their career as a full-time artist actually kicked off because they were able to leverage their art’s popularity on Instagram. 

“I absolutely love managing my social media,” Wednesday says. “My whole career was born from it. I created 100 artworks in 100 days to launch my Instagram account. So I've always been quite good at keeping up with posting.” 

“Over the years I've learned to slow down a bit, in search of more rest. That's how I maintain a bit more balance with work and socials. I've learned that my audience is happy to wait for more art.” Currently, that audience includes over 315,000 followers on Wednesday’s Instagram

As they’ve shared their art and engaged with their social following over the years, it’s important to Wednesday to remind themself of these three crucial lessons: 

  1. “Not every artwork is going to be popular—and that’s okay.”

  2. “Sometimes you’re going to get it wrong—and that’s okay.”

  3. “Not everyone is going to like you—and that’s okay.”

Want to launch your own freelance creative career? 

As an experienced working artist, here’s Wednesday’s advice for you: 

  1. Your rest matters. You aren’t a machine. Create art because you’re inspired to, not because you need to feed the content machine. 

  2. Consistency is key. Find your style and pattern that feels comfortable for you, and stick with that. 

  3. Connect with other artists online, and find your community. 


Inspired by Wednesday’s story? Start building your own brand on Squarespace. 

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